Sulfuric Acid → 3,7-Dimethyloct-3-enoic acid

HRID 392843ノート

反応式

HRID 392843 の反応式
S(=O)(=O)(O)[OH:2].[CH3:6]/[C:7](=[CH:11]\[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])/[CH2:8][CH2:9][OH:10]>O.CC(C)=O.O.O.O.[Cr]>[CH3:6][C:7](=[CH:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][C:9]([OH:2])=[O:10]

参加物

6

反応物 2

HCID 1118Sulfuric AcidHCID 22661166HCID 22661166、化合物

生成物 1

HCID 713655083,7-Dimethyloct-3-enoic acid

試薬・触媒・溶媒 3

HCID 14787Chromium trihydroxide触媒HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A solution of 8.84 g (88.4 mmol, 3 eq) of chromium VI oxide in 25 mL of water in the presence of 8.2 mL of 95% sulphuric acid is added to a solution of 4.6 g (29.5 mmol, 1 eq) of (E)-3,7-dimethyloct-3-enol in 250 mL of acetone, at 0° C., while maintaining the temperature at 0° C. After addition, the reaction mixture is stirred for 15 minutes at 0° C. and the reaction is then quenched by adding 250 mL of water. The reaction medium is extracted with 2×250 mL of diethyl ether. The organic phases are combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate, and the residue is then filtered through silica gel: eluent (95/5→75/25 Cy/EtOAc).

後処理

  1. additionAfter addition
  2. customthe reaction is then quenched
  3. additionby adding 250 mL of water
  4. extractionThe reaction medium is extracted with 2×250 mL of diethyl ether
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationthe residue is then filtered through silica gel

出典と根拠

ORDレコード
ord-c8de4d884ec946e2a73d0ce20047b62b
出典データセット
uspto-grants-2004_10
特許番号
US06803382B2

反応ノート

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